Chicago Style Management

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Chicago Style Management Property management company in Chicago

Chicago Style Management was formed to assist in the investment of property in the Chicagoland area, by people who invest and live in the city. Our logo has 4 stars similar to the Chicago flag and stands for our 4 points of emphasis: Investors, Tenants, Employees, City

Chicago Property Management vs. Self-Managing: What Does It Actually Cost You?“Why would I pay a property manager when I...
10/06/2026

Chicago Property Management vs. Self-Managing: What Does It Actually Cost You?

“Why would I pay a property manager when I can collect the rent myself?”

It is a fair question. If you own a rental property in Chicago, keeping expenses under control matters. Management is another line on the budget, and you should understand what you are getting for it.

But collecting rent is only one part of managing a property.

There are showings, maintenance calls, contractor appointments, lease renewals, payment follow-ups, and records to keep. Someone has to do that work. When you self-manage, that someone is you.

Self-managing can save money. Professional management can save time and improve how a property operates. The right choice starts with comparing the full cost of both.

What Does Professional Property Management Cost?

Management companies structure their fees differently. Some charge a percentage of collected rent. Others use a flat ...READ MORE AT OUR BLOG: https://www.chicagostylemanagement.com/blog/chicago-property-management-vs-self-managing-what-does-it-actually-cost-you

10/06/2026

Chicago City Council got WILD.

Public comments took a serious turn and the reaction says it all.

For Chicago landlords, property owners and real estate investors, what happens at City Hall matters.

Stay informed on Chicago real estate, housing policy and issues affecting rental property owners.

Follow for more Chicago landlord & real estate content.

Best Chicago Neighborhoods for Rental InvestmentsWhere should you buy a rental property in Chicago?The answer depends on...
09/29/2026

Best Chicago Neighborhoods for Rental Investments

Where should you buy a rental property in Chicago?

The answer depends on what you need that property to do. You might be looking for monthly cash flow, a building to improve over time, or a two-flat where you can live in one unit and rent the other.

At Chicago Style Management, we recommend starting with a neighborhood shortlist, then getting specific about the property. The purchase price, achievable rent, building condition, and operating expenses ultimately determine whether the investment makes sense.

Woodlawn, Bronzeville, South Shore, Chatham, Bridgeport, Hyde Park, and Albany Park are seven areas worth researching. This is our shortlist for different investment strategies, rather than a statistical ranking of returns.

Woodlawn
Woodlawn is worth considering for investors planning to hold a property for the long term. Its location near the University of Chicago and Jackson Park gives buyers concrete amenities to evaluate. The area's cultural destinations include the university's Logan Center.

The Obama Presidential Center in Jackson Park adds another nearby destination. However, the presence of a major institution does not establish what a particular apartment will rent for.

When evaluating a Woodlawn property, check the actual distance to transportation and amenities. Compare apartments with similar bedrooms, finishes, laundry, parking, and utility arrangements. A newly renovated unit several blocks away may face different competition from the building you are buying.

Our investment perspective: Consider Woodlawn for a long-term hold, but make the purchase work on supportable rents today. Future appreciation should be a possible benefit, not a requirement for paying the bills.

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look with the injury list our beloved Bears may have a rough time tonight but we are still gonna watch with our friends ...
09/28/2026

look with the injury list our beloved Bears may have a rough time tonight but we are still gonna watch with our friends and family and hope for the best, Lets go Bears!! If you are to busy to watch the game its time to stop managing your own properties and hire Chicago Style Management to handle your investments.

09/26/2026

Great conversations, great people, and a great time at the NBOA summer soiree event! 🎉

We enjoyed connecting with other real estate professionals, sharing ideas, and talking about the Chicago property management industry.

Events like NBOA are a great reminder of how valuable it is to build relationships and stay connected with the people shaping the real estate and property management community.

Thank you to everyone who made it such a great event!

we are a little late on this one, but the South Side's premier property management company would like to congratulate th...
09/26/2026

we are a little late on this one, but the South Side's premier property management company would like to congratulate the South Side's premier baseball team on clinching a playoff berth

09/25/2026

Condo, house, or 4-unit, what would you buy for your FIRST investment property?

PRO Ordinance moves forward in Chicago housing committeeChicago's Renter Protection Fight Heads to a Final Vote — But No...
09/23/2026

PRO Ordinance moves forward in Chicago housing committee

Chicago's Renter Protection Fight Heads to a Final Vote — But Not the One Landlords Feared

Chicago's yearlong battle over how far the city should go to protect tenants is about to reach a milestone. The City Council is set to cast its final vote on Mayor Brandon Johnson's Protecting Renters Ordinance (PRO) on September 23, closing out months of hearings, rallies, and closed-door negotiations between City Hall, tenant organizers, and the real estate industry.

But the version of the ordinance headed to the floor looks noticeably different from the one Johnson first unveiled. In the weeks leading up to last week's Housing Committee vote, the mayor's office quietly dropped two of the bill's most contested provisions: a "just cause" eviction requirement and mandatory relocation payments for displaced tenants. For landlords and property managers who have been watching this fight closely, that's the headline.

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09/23/2026

You can only use ONE metric to evaluate a property.

Which one are you choosing?

📊 Comparables
💰 Rent-to-value
📈 Cap rate

For single-family investments, there’s a good argument for looking at these numbers differently.

What would you use first?


Happy weekendOur prediction Da Bears 47 Vikings 21If your to busy dealing with tenants to watch this historic bears offe...
09/18/2026

Happy weekend

Our prediction Da Bears 47 Vikings 21

If your to busy dealing with tenants to watch this historic bears offense go to chicagostylemanagement.com and get a quote to have us manage your chicago investment property so you can enjoy this super bowl run

Address

3341 S Lituanica Avenue
Chicago, IL
60608

Opening Hours

Monday 9am - 5pm
Tuesday 9am - 5pm
Wednesday 9am - 5pm
Thursday 9am - 5pm
Friday 9am - 5pm

Telephone

+12246015415

Website

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